ChemInform Abstract: THIOESTERBROMIDE DER AETHYLTHIOPHOSPHONIGSAEURE

Потапов, А. П.; Красильникова, Е. А.; Razumov, A. I.

doi:10.1002/chin.197027018

Cited by 3 publications

(4 citation statements)

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“…TLC was carried out on Silufol UV-254 sheets in the following chromatographic systems: (A) 3 : 1 benzene-dioxane, (B) 5 : 1 hexane-dioxane, and (C) 10 : 1 hexane-dioxane. The phosphorus-containing substances were detected by Molybdenum Blue [30]; the sulfur-containing substances, with 1% aqueous solution of silver nitrate [31]; and by heating. Isopropylidene derivative of trimethylolpentane (I) was prepared by method [32], bicyclophosphite of trimethylolpentane (XVIII), by method [33], hexaethyl triamidophosphite (II), by method [34], and ethylene chlorophosphite (X), by method [35].…”

Section: Resultsmentioning

confidence: 99%

“…The product (VI) was obtained as an oily liquid; yield 0.41 g (52%); R f 0.5 (C); 1 H NMR: 0.87 [9 H, t, CH 3 (CH 2 ) 10 + CH 3 (CH 2 ) 3 2,2-Di(myristoyloxymethyl)hexane-1-ol bis(diethylamido)selenophosphate (VIII) was prepared as described for (VI) from selenophosphate (V) (0.46 g), myristoyl chloride (0.5 g), and anhydrous zinc chloride (5 mg). The product was prepared as an oily liquid in yield of 0.44 g (53%); R f 0.5 (C); its 1 H NMR spectrum was similar to that of (VI); 31 2,2-Di(stearoyloxymethyl)hexane-1-ol bis(diethylamido)selenophosphate (IX) was prepared as described for (VI) from selenophosphate (V) (0.46 g), stearoyl chloride (0.6 g), and anhydrous zinc chloride (5 mg); yield 0.5 g (52.5%); mp 34-36°C (from ether); R f 0.5 (C); its 1 H NMR spectrum was similar to that of (VI); 31 …”

Section: 2-di(myristoyloxymethyl)hexane-1-ol Bis(diethylamido)thiopmentioning

confidence: 99%

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The Synthesis of Thio- and Selenoanalogues of Phospholipids on the Basis of 2-Butyl-2-Hydroxymethyl-1,3-Propanediol

Савин

Kutsemako

2005

Russ J Bioorg Chem

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New analogues of nonglycerol polyol phospholipids were prepared on the basis of 1,1,1-trimethylolethane. Amidophosphites and cyclophosphites of the isopropylidene derivative of this polyol were intermediates in the syntheses. They were treated with sulfur or selenium. Phosphoacetals were converted into lipids by the direct acylation with higher fatty acid chlorides. The triol bicyclophosphite was also used in the lipid syntheses. It was directly acylated at the oxygen atom, the resulting acylpolyol of chlorophosphite was then converted into phospholipids by alcoholysis and subsequent treatment with sulfur.

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Section: Resultsmentioning

confidence: 99%

Section: 2-di(myristoyloxymethyl)hexane-1-ol Bis(diethylamido)thiopmentioning

confidence: 99%

The Synthesis of Thio- and Selenoanalogues of Phospholipids on the Basis of 2-Butyl-2-Hydroxymethyl-1,3-Propanediol

Савин

Kutsemako

2005

Russ J Bioorg Chem

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“…Silica gel L (100/250 μm) was used for column chromatography. TLC analysis was performed using Silufol UV-254 plates [benzene-dioxane, 3 : 1 (A); benzene-dioxane, 10 : 1 (B); hexane-dioxane, 3 : 1 (C)]; phosphoruscontaining substances were detected by treatment with Molybdenum Blue [28], and sulfur-containing substances, by treatment with a 1% aqueous solution of silver nitrate [29] and by calcination. All syntheses with phosphorus(III) compounds were performed under dry argon.…”

Section: Methodsmentioning

confidence: 99%

2-Hydroxymethyl-2-propyl-1,3-propanediol in the Synthesis of Phospholipids

Савин

Kamneva

2005

Russ J Org Chem

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New representatives of nonglycerol polyol phospholipids were synthesized from 2-hydroxymethyl-2-propyl-1,3-propanediol through intermediate phosphoramidites and cyclic phosphites obtained from isopropylidene derivative of the title triol. Treatment of these intermediate products with sulfur or selenium afforded the corresponding thio-and selenophosphates which were converted into lipids by direct acylation with higher carboxylic acid chlorides.* For short communication, see [1]. Phospholipids in which the alcohol fragment is not glycerol but other polyols are very promising for use in biochemical and biophysical studies. Therefore, development of methods for synthesizing such compounds is an important problem [2,3]. Phospholipids modified at the alcoholic fragment were previously synthesized on the basis of 2-hydroxymethyl-2-methyl-1,3-propanediol (metriol) and 1,2,4-butanetriol [4], D-mannite and D-glucite [5], 1,2,5-pentanetriol [6], and isomeric 1,2,3-cyclopentanetriols [7-12]. The products were successfully used in studies on membrane models [13,14] and catalytic activity of some phospholipases [4,8,15]. However, the above syntheses were performed with the use of phosphorus(V) compounds as phosphorylating agents, and the yields of the target products were not high.New methods of synthesis of nonglycerol polyol phospholipids involve phosphorus(III) compounds as phosphorylating agents [16,17], which make it possible to obtain not only phospholipids but also their sulfur-and selenium-containing analogs. The latter attract interest as models for various biophysical studies using NMR spectroscopy. Some advances in the synthesis of lipids by the phosphite technique have been reported [18][19][20][21][22][23][24][25].In continuation of our previous studies in this line, the present communication reports on the synthesis of previously unknown phospholipids on the basis of 2-hydroxymethyl-2-propyl-1,3-propanediol. As initial compound we used readily accessible 5-hydroxymethyl-2,2-dimethyl-5-propyl-1,3-dioxane (I) which was subjected to phosphorylation with hexaethylphosphorous triamide (II) to obtain compound III (Scheme 1). In order to raise the yield of the target product, 3 equiv of triamide II was used, and excess reagent was distilled off when the reaction was complete. The formation of phosphorodiamidite III was monitored by 31 P NMR spectroscopy: a singlet at δ P 134 ppm appeared in the spectrum of the reaction mixture. Scheme 1. O O Pr HO Me Me I + P(NEt 2 ) 3 II O O Pr OP(NEt 2 ) 2 Me Me IIICompound III was converted (without isolation and purification) to the corresponding thio-and selenophosphates IV and V by treatment with sulfur or selenium, respectively (Scheme 2). The transformation of phosphorodiamidite III into phosphorus(V) compounds IV and V was monitored by TLC and 31 P NMR spectroscopy. The 31 P NMR spectra of the reaction mixtures contained singlets at δ P 79 (IV) and 81 ppm (V). In addition, the 31 P NMR spectrum of selenium derivative V contained satellites due to 31 P-77 Se coupling with a con...

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“…Color reactions for thiols and sulfoxides on thin-layer chromatograms have been described (484,1591). Organophosphorus compounds (see also under Pesticides) have been studied by chromatographic techniques: paper and thin-layer chromatography of organo P(III) and P(V) acids has been reviewed (1102) and studied (1103); diand monoesters of phosphoric acid have been resolved by TLC (1341); neutral organophosphorus compounds have been separated by TLC (794); phosphines and derivatives by TLC (474); zinc dialkyl dithiophosphates have been analyzed by TLC (578); nitrogenated derivatives of phosphorus have been separated by TLC (907); exo-trimethy lenenorborny 1-2 -exophosphates have been separated on columns of Sephadex LH-20 (1410). Aminoalkylphosphonates separated by paper chromatography have been detected with a ninhydrinmolybdate spray reagent system (1179).…”

Section: Yellow Food Dyes Have Been Identifiedmentioning

confidence: 99%